A Novel Approach to Pyrrolo[2,1-b]thiazoles

Anton V. Tverdokhlebov; Elizaveta V. Resnyanska; Andrey A. Tolmachev; Alexander P. Andrushko

doi:10.1055/s-2003-42451

PAPER

A Novel Approach to Pyrrolo[2,1-b]thiazoles

Anton V. Tverdokhlebov*^a, Elizaveta V. Resnyanska^a, Andrey A. Tolmachev^b, Alexander P. Andrushko^a
^a Enamine Ltd. Co., I. Kudry str. 31, apt.17, 02042, Kiev, Ukraine
^b Kiev National Taras Shevchenko University, Volodimirska str., 62, 01033, Kiev, Ukraine
e-Mail: atver@mail.univ.kiev.ua;

Abstract

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Abstract

5-Aroyl-2-(dimethylamino)methylidene-2,3-dihydro-3-oxopyrrolo[2,1-b]thiazole-7-carboxylic acid esters, -7-carbonitriles and corresponding 7-hetaryl substituted derivatives were prepared. Thus, the substituted acetonitriles (XCH₂CN, where X = CO₂R, CN, hetaryl) were treated with mercaptoacetic acid yielding 2-(X-methylidene)thiazolidin-4-ones, which were N-alkylated with phenacyl bromides. Further formylation of the obtained compounds with excess of DMF·POCl₃ complex led to the above mentioned pyrrolo[2,1-b]thiazoles.

Key words

alkylations - heterocycles - pyrrolo[2,1-b]thiazoles - ring closure - 4-thiazolidinones

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References

<A NAME="RZ06403SS-1A">1a</A> Khalil EM. Pradhan A. Ojala WH. Cleason WB. Mishra RK. Johnson RL. J. Med. Chem. 1999, 42: 2977

<A NAME="RZ06403SS-1B">1b</A> Subashinghe NL. Bontems RJ. McIntee E. Mishra RK. Johnson RL. J. Med. Chem. 1993, 36: 2356

<A NAME="RZ06403SS-2A">2a</A> Suzuki N, Nakayama A, Saijo T, Hasegawa M, and Yokohama S. inventors; Japanese Patent 04145086. ; Chem. Abstr. 1992, 117, 212487

<A NAME="RZ06403SS-2B">2b</A> Suzuki N, Nakayama A, Hosokami TC, Hasegawa M, and Yokohama S. inventors; Spanish Patent 410224. ; Chem. Abstr. 1991, 115, 49668

<A NAME="RZ06403SS-2C">2c</A> Suzuki N, Nakayama A, Hasegawa M, Yokohama S, and Saijo T. inventors; Japanese Patent 04261186. ; Chem. Abstr. 1993, 118, 213095

<A NAME="RZ06403SS-2D">2d</A> Suzuki N, Nakayama A, Saijo T, Hasegawa M, Yokohama S, and Otsubo E. inventors; Japanese Patent 04208290. ; Chem. Abstr. 1993, 118, 124527

<A NAME="RZ06403SS-2E">2e</A> Hasegawa M. Nakayama A. Yokohama S. Hosokami T. Kurebayashi Y. Ikeda T. Shimoto Y. Ide S. Honda Y. Suzuki N. Chem. Pharm. Bull. 1995, 43: 1125

<A NAME="RZ06403SS-3A">3a</A> Padwa A. Chiacchio U. Venkatramanan MK. J. Chem. Soc., Chem. Commun. 1985, 1108

<A NAME="RZ06403SS-3B">3b</A> Tsuge O. Kanemasa S. Takenaka S. Bull. Chem. Soc. Jpn. 1985, 3137

<A NAME="RZ06403SS-3C">3c</A> Tsuge O. Kanemasa S. Takenaka S. Heterocycles 1983, 20: 1907

<A NAME="RZ06403SS-3D">3d</A> Kraus GA. Nagy JO. Tetrahedron 1985, 41: 3537

<A NAME="RZ06403SS-3E">3e</A> Kraus GA. Nagy JO. Tetrahedron Lett. 1981, 22: 2727

<A NAME="RZ06403SS-4A">4a</A> Abe N. Nishiwaki T. Komoto N. Bull. Chem. Soc. Jpn. 1980, 53: 3308

<A NAME="RZ06403SS-4B">4b</A> Abe N. Nishiwaki T. Komoto N. Chem. Lett. 1980, 223

<A NAME="RZ06403SS-5A">5a</A> Farbe JL, Farge D, James C, and Lave D. inventors; Spanish Patent 147317. ; Chem. Abstr. 1985, 103, 160500

<A NAME="RZ06403SS-5B">5b</A> Lalezari I. Schwartz EL. J. Med. Chem. 1988, 31: 1427

<A NAME="RZ06403SS-5C">5c</A> Bacque E, Bashiardes G, Dereu N, and Nemecek C. inventors; PCT Int. Appl. WO 9700073. ; Chem. Abstr. 1997, 126, 157394

<A NAME="RZ06403SS-6A">6a</A> Volovenko YuM. Volovnenko TA. Tverdokhlebov AV. Chem. Heterocycl. Compd. (Engl. Transl.) 2001, 37: 1011

<A NAME="RZ06403SS-6B">6b</A> Volovenko YuM. Tverdokhlebov AV. Gorulya AP. Shishkina SV. Zubatyuk RI. Shishkin OV. Eur. J. Org. Chem. 2002, 4: 663

<A NAME="RZ06403SS-7A">7a</A> Meyer H. Liebigs Ann. Chem. 1981, 1534

<A NAME="RZ06403SS-7B">7b</A> Gupta AK. Ila H. Junjappa H. Synthesis 1988, 284

<A NAME="RZ06403SS-7C">7c</A> Gupta AK. Chakrasali RT. Ila H. Junjappa H. Synthesis 1989, 141

<A NAME="RZ06403SS-7D">7d</A> El-Shafei AK. El-Sayed AM. Abdel-Ghany H. Gazz. Chim. Ital. 1990, 120: 193

<A NAME="RZ06403SS-7E">7e</A> Schafer H. Gewald K. J. Prakt. Chem. 1974, 316: 684

<A NAME="RZ06403SS-8A">8a</A> Elnagdi MH. Elmoghayar RMH. Hammam AEFG. Khallaf SA. J. Heterocycl. Chem. 1979, 16: 1541

<A NAME="RZ06403SS-8B">8b</A> Satzinger G. Liebigs Ann. Chem. 1978, 473

<A NAME="RZ06403SS-8C">8c</A> Satzinger G. Liebigs Ann. Chem. 1963, 151

<A NAME="RZ06403SS-8D">8d</A> Isidor JL. McKee RL. J. Org. Chem. 1973, 38: 3615

<A NAME="RZ06403SS-8E">8e</A> Elnagdi MH. Khalifa MAE. Ibraheim MKA. Elmoghayar RMH. J. Heterocycl. Chem. 1981, 18: 877

<A NAME="RZ06403SS-8F">8f</A> El-Shafei AK. El-Sayed AM. Soliman AM. Gazz. Chim. Ital. 1987, 117: 385

<A NAME="RZ06403SS-9A">9a</A> Knoll A, Paetzel M, and Liebscher J. inventors; German Patent (East) 262863. ; Chem. Abstr. 1989, 111, 153789

<A NAME="RZ06403SS-9B">9b</A> Knoll A. Liebscher J. Z. Chem. 1988, 28: 214

<A NAME="RZ06403SS-10A">10a</A> Coulton S. Southgate R. J. Chem. Soc., Perkin Trans. 1 1992, 961

<A NAME="RZ06403SS-10B">10b</A> Cheeseman GWH. Hawi AA. J. Heterocycl. Chem. 1983, 20: 591

<A NAME="RZ06403SS-11">11</A> Balls AK. Kohler F. Ber. Dtsch. Chem. Ges. 1931, 64: 34

<A NAME="RZ06403SS-12">12</A> Elnagdi MH. Abdallah SO. Ghoneim KM. Ebied EM. Kassab KN. J. Chem. Res., Miniprint 1997, 2: 375